# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_SACT-ACT_Form1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfacetamide-acetamide 1:1' ; _chemical_name_common Sulfacetamide-acetamide _chemical_melting_point 379 _chemical_formula_moiety 'C8 H10 N2 O3 S . C2 H5 N O' _chemical_formula_sum 'C10 H15 N3 O4 S' _chemical_formula_weight 273.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2134(6) _cell_length_b 7.7976(4) _cell_length_c 16.1280(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.260(5) _cell_angle_gamma 90.00 _cell_volume 1372.59(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1289 _cell_measurement_theta_min 2.8220 _cell_measurement_theta_max 26.3125 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9166 _exptl_absorpt_correction_T_max 0.9710 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3291 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5157 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2334 _reflns_number_gt 1606 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The terminal methyl carbon (C10 atom) of acetamide coformer showed relatively larger ADPs, probably due to larger librations of the terminal group. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.3303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2334 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18878(7) 0.16134(10) 0.58254(4) 0.0511(3) Uani 1 1 d . . . O1 O 0.07515(19) 0.2499(3) 0.56284(13) 0.0645(6) Uani 1 1 d . . . O2 O 0.2660(2) 0.1683(3) 0.52351(13) 0.0703(7) Uani 1 1 d . . . C1 C 0.4024(3) 0.3268(4) 0.84213(18) 0.0482(7) Uani 1 1 d . . . C6 C 0.2762(3) 0.3544(4) 0.81728(18) 0.0501(8) Uani 1 1 d . . . H6 H 0.2359 0.4080 0.8545 0.060 Uiso 1 1 calc R . . C4 C 0.2706(3) 0.2266(4) 0.68262(17) 0.0430(7) Uani 1 1 d . . . C3 C 0.3961(3) 0.1984(4) 0.70575(19) 0.0499(8) Uani 1 1 d . . . H3 H 0.4359 0.1451 0.6681 0.060 Uiso 1 1 calc R . . C5 C 0.2113(3) 0.3036(4) 0.73872(18) 0.0480(7) Uani 1 1 d . . . H5 H 0.1271 0.3210 0.7231 0.058 Uiso 1 1 calc R . . C2 C 0.4606(3) 0.2496(4) 0.78442(19) 0.0544(8) Uani 1 1 d . . . H2 H 0.5449 0.2324 0.7996 0.065 Uiso 1 1 calc R . . N1 N 0.4664(3) 0.3789(5) 0.9206(2) 0.0695(9) Uani 1 1 d . . . O3 O 0.0560(2) -0.0274(3) 0.69304(15) 0.0735(7) Uani 1 1 d . . . N2 N 0.1612(3) -0.0457(4) 0.59057(18) 0.0551(8) Uani 1 1 d . . . C7 C 0.0968(3) -0.1153(4) 0.6446(2) 0.0576(9) Uani 1 1 d . . . C8 C 0.0844(4) -0.3045(4) 0.6389(2) 0.0882(13) Uani 1 1 d . . . H8A H 0.0586 -0.3470 0.6878 0.132 Uiso 1 1 calc R . . H8B H 0.1619 -0.3545 0.6369 0.132 Uiso 1 1 calc R . . H8C H 0.0246 -0.3346 0.5882 0.132 Uiso 1 1 calc R . . O4 O 0.7185(2) 0.2499(4) 0.50406(18) 0.0874(9) Uani 1 1 d . . . C9 C 0.7424(3) 0.3209(5) 0.5738(3) 0.0656(10) Uani 1 1 d . . . N3 N 0.8539(3) 0.3287(6) 0.6217(3) 0.1002(13) Uani 1 1 d D . . C10 C 0.6446(4) 0.3975(7) 0.6082(4) 0.136(2) Uani 1 1 d . . . H10A H 0.6522 0.5202 0.6083 0.204 Uiso 1 1 calc R . . H10B H 0.6512 0.3578 0.6654 0.204 Uiso 1 1 calc R . . H10C H 0.5665 0.3648 0.5735 0.204 Uiso 1 1 calc R . . H1B H 0.543(3) 0.334(5) 0.937(2) 0.089(13) Uiso 1 1 d . . . H2A H 0.190(3) -0.100(4) 0.561(2) 0.057(11) Uiso 1 1 d . . . H1A H 0.425(4) 0.393(5) 0.957(3) 0.099(16) Uiso 1 1 d . . . H3B H 0.857(5) 0.399(6) 0.666(2) 0.16(2) Uiso 1 1 d D . . H3A H 0.923(3) 0.290(7) 0.605(3) 0.15(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0584(5) 0.0626(6) 0.0320(4) -0.0025(4) 0.0096(4) 0.0003(4) O1 0.0624(13) 0.0762(16) 0.0482(13) 0.0038(11) -0.0010(11) 0.0141(12) O2 0.0833(15) 0.0972(19) 0.0378(12) -0.0048(11) 0.0293(12) -0.0091(13) C1 0.0519(17) 0.0512(19) 0.0413(17) -0.0055(14) 0.0104(15) -0.0131(15) C6 0.0577(18) 0.057(2) 0.0387(16) -0.0087(14) 0.0172(15) 0.0025(15) C4 0.0512(16) 0.0463(18) 0.0325(15) -0.0040(12) 0.0117(14) -0.0001(14) C3 0.0520(17) 0.056(2) 0.0469(18) -0.0062(14) 0.0216(15) -0.0031(15) C5 0.0478(16) 0.0534(19) 0.0419(17) -0.0013(14) 0.0085(14) 0.0062(14) C2 0.0413(16) 0.071(2) 0.0511(19) -0.0036(16) 0.0117(15) -0.0056(15) N1 0.0588(19) 0.100(3) 0.0474(18) -0.0196(17) 0.0079(17) -0.0179(19) O3 0.0906(17) 0.0738(17) 0.0663(15) -0.0077(13) 0.0390(14) -0.0110(13) N2 0.0628(17) 0.0579(18) 0.0457(16) -0.0159(14) 0.0148(14) -0.0009(15) C7 0.067(2) 0.058(2) 0.0450(19) 0.0003(16) 0.0064(18) -0.0081(17) C8 0.129(3) 0.056(2) 0.075(3) 0.0063(19) 0.013(3) -0.007(2) O4 0.0642(14) 0.110(2) 0.0865(19) -0.0515(16) 0.0141(14) 0.0069(14) C9 0.063(2) 0.063(2) 0.078(3) -0.0220(19) 0.030(2) -0.0038(18) N3 0.067(2) 0.152(4) 0.082(3) -0.045(3) 0.017(2) -0.004(2) C10 0.101(3) 0.160(5) 0.159(5) -0.084(4) 0.053(3) 0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.420(2) . ? S1 O2 1.427(2) . ? S1 N2 1.654(3) . ? S1 C4 1.740(3) . ? C1 N1 1.366(4) . ? C1 C2 1.390(4) . ? C1 C6 1.396(4) . ? C6 C5 1.367(4) . ? C6 H6 0.9300 . ? C4 C5 1.377(4) . ? C4 C3 1.388(4) . ? C3 C2 1.368(4) . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? N1 H1B 0.91(4) . ? N1 H1A 0.83(4) . ? O3 C7 1.206(4) . ? N2 C7 1.366(4) . ? N2 H2A 0.77(3) . ? C7 C8 1.483(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O4 C9 1.227(4) . ? C9 N3 1.312(5) . ? C9 C10 1.464(5) . ? N3 H3B 0.90(2) . ? N3 H3A 0.924(19) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.88(14) . . ? O1 S1 N2 108.53(14) . . ? O2 S1 N2 104.02(15) . . ? O1 S1 C4 108.71(14) . . ? O2 S1 C4 109.64(14) . . ? N2 S1 C4 106.32(14) . . ? N1 C1 C2 121.4(3) . . ? N1 C1 C6 120.2(3) . . ? C2 C1 C6 118.4(3) . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 S1 120.4(2) . . ? C3 C4 S1 119.3(2) . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C3 C2 C1 121.2(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C1 N1 H1B 115(2) . . ? C1 N1 H1A 116(3) . . ? H1B N1 H1A 119(4) . . ? C7 N2 S1 125.0(3) . . ? C7 N2 H2A 123(3) . . ? S1 N2 H2A 112(3) . . ? O3 C7 N2 121.5(3) . . ? O3 C7 C8 124.2(3) . . ? N2 C7 C8 114.3(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O4 C9 N3 122.6(3) . . ? O4 C9 C10 120.4(3) . . ? N3 C9 C10 117.0(4) . . ? C9 N3 H3B 111(3) . . ? C9 N3 H3A 125(3) . . ? H3B N3 H3A 123(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.209 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 941617' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_SACT-ACT_Form2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Sulfacetamide-acetamide 1:1' ; _chemical_name_common Sulfacetamide-acetamide _chemical_melting_point 376 _chemical_formula_moiety 'C8 H10 N2 O3 S . C2 H5 N O' _chemical_formula_sum 'C10 H15 N3 O4 S' _chemical_formula_weight 273.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.2392(16) _cell_length_b 8.4705(4) _cell_length_c 14.7710(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.056(8) _cell_angle_gamma 90.00 _cell_volume 2660.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1205 _cell_measurement_theta_min 2.8175 _cell_measurement_theta_max 26.3103 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9208 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3291 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4513 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2256 _reflns_number_gt 1741 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+1.4328P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2256 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.13763(3) 1.16112(7) 0.40334(5) 0.0461(2) Uani 1 1 d . . . C4 C 0.09466(12) 0.9876(3) 0.38511(18) 0.0397(6) Uani 1 1 d . . . C7 C 0.20192(12) 1.0818(3) 0.58039(19) 0.0444(6) Uani 1 1 d . . . C5 C 0.12191(12) 0.8478(3) 0.36835(18) 0.0406(6) Uani 1 1 d . . . H5 H 0.1626 0.8483 0.3632 0.049 Uiso 1 1 calc R . . C3 C 0.03357(13) 0.9862(3) 0.3913(2) 0.0505(7) Uani 1 1 d . . . H3 H 0.0146 1.0801 0.4009 0.061 Uiso 1 1 calc R . . C6 C 0.08930(12) 0.7092(3) 0.35937(18) 0.0439(6) Uani 1 1 d . . . H6 H 0.1077 0.6163 0.3469 0.053 Uiso 1 1 calc R . . C9 C 0.35358(12) 0.9130(3) 0.40107(18) 0.0432(6) Uani 1 1 d . . . C1 C 0.02874(12) 0.7053(3) 0.36868(18) 0.0437(6) Uani 1 1 d . . . C2 C 0.00118(13) 0.8474(3) 0.3833(2) 0.0522(7) Uani 1 1 d . . . H2 H -0.0397 0.8476 0.3876 0.063 Uiso 1 1 calc R . . C10 C 0.38922(14) 0.7776(3) 0.3776(2) 0.0600(8) Uani 1 1 d . . . H10A H 0.3887 0.7847 0.3125 0.090 Uiso 1 1 calc R . . H10B H 0.3700 0.6802 0.3876 0.090 Uiso 1 1 calc R . . H10C H 0.4319 0.7806 0.4176 0.090 Uiso 1 1 calc R . . C8 C 0.21489(17) 1.1186(4) 0.6832(2) 0.0667(9) Uani 1 1 d . . . H8A H 0.1863 1.0607 0.7083 0.100 Uiso 1 1 calc R . . H8B H 0.2094 1.2297 0.6910 0.100 Uiso 1 1 calc R . . H8C H 0.2573 1.0892 0.7164 0.100 Uiso 1 1 calc R . . N2 N 0.16300(11) 1.1847(3) 0.51973(17) 0.0465(6) Uani 1 1 d . . . O1 O 0.19088(9) 1.1424(2) 0.36903(14) 0.0561(5) Uani 1 1 d . . . O3 O 0.22260(9) 0.9654(2) 0.55161(14) 0.0532(5) Uani 1 1 d . . . N1 N -0.00220(15) 0.5666(3) 0.3640(2) 0.0646(8) Uani 1 1 d . . . N3 N 0.30228(12) 0.8792(4) 0.42383(19) 0.0531(7) Uani 1 1 d . . . O2 O 0.09683(10) 1.2925(2) 0.37216(15) 0.0672(6) Uani 1 1 d . . . O4 O 0.37190(10) 1.0498(2) 0.39753(17) 0.0672(6) Uani 1 1 d . . . H2A H 0.1522(13) 1.262(3) 0.542(2) 0.052(9) Uiso 1 1 d . . . H1B H -0.0364(16) 0.564(3) 0.375(2) 0.060(10) Uiso 1 1 d . . . H1A H 0.0198(17) 0.481(4) 0.358(3) 0.088(12) Uiso 1 1 d . . . H3A H 0.2812(14) 0.952(4) 0.439(2) 0.062(10) Uiso 1 1 d . . . H3B H 0.2928(14) 0.788(4) 0.429(2) 0.061(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0557(4) 0.0347(4) 0.0494(4) 0.0013(3) 0.0178(3) -0.0018(3) C4 0.0395(14) 0.0368(13) 0.0421(15) -0.0026(11) 0.0108(12) -0.0009(11) C7 0.0466(15) 0.0398(14) 0.0499(17) -0.0032(13) 0.0189(14) -0.0145(13) C5 0.0343(13) 0.0444(14) 0.0448(15) -0.0057(12) 0.0142(12) 0.0010(11) C3 0.0446(16) 0.0436(15) 0.0645(19) -0.0055(14) 0.0178(14) 0.0077(12) C6 0.0421(15) 0.0386(13) 0.0518(16) -0.0070(12) 0.0149(13) 0.0024(12) C9 0.0456(15) 0.0455(15) 0.0394(15) -0.0044(12) 0.0141(12) 0.0002(13) C1 0.0422(15) 0.0433(14) 0.0444(15) 0.0002(12) 0.0108(13) -0.0052(12) C2 0.0364(14) 0.0573(17) 0.0653(19) -0.0033(15) 0.0185(14) -0.0009(13) C10 0.0647(19) 0.0498(16) 0.076(2) -0.0060(15) 0.0367(17) 0.0035(15) C8 0.087(2) 0.0688(19) 0.0471(18) -0.0038(15) 0.0239(17) -0.0242(17) N2 0.0538(14) 0.0349(12) 0.0545(15) -0.0110(12) 0.0216(12) -0.0041(11) O1 0.0644(13) 0.0530(11) 0.0608(13) -0.0019(9) 0.0339(11) -0.0126(9) O3 0.0574(12) 0.0452(10) 0.0589(12) 0.0009(9) 0.0200(10) 0.0015(9) N1 0.0533(17) 0.0503(16) 0.096(2) 0.0002(15) 0.0307(17) -0.0088(14) N3 0.0493(15) 0.0494(16) 0.0659(18) 0.0017(14) 0.0250(13) 0.0054(13) O2 0.0792(15) 0.0413(10) 0.0752(15) 0.0090(10) 0.0135(12) 0.0094(10) O4 0.0698(14) 0.0420(11) 0.1046(18) -0.0168(11) 0.0485(13) -0.0089(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4241(19) . ? S1 O1 1.4270(19) . ? S1 N2 1.657(2) . ? S1 C4 1.730(2) . ? C4 C5 1.385(3) . ? C4 C3 1.388(4) . ? C7 O3 1.216(3) . ? C7 N2 1.363(4) . ? C7 C8 1.493(4) . ? C5 C6 1.366(3) . ? C5 H5 0.9300 . ? C3 C2 1.366(4) . ? C3 H3 0.9300 . ? C6 C1 1.394(3) . ? C6 H6 0.9300 . ? C9 O4 1.234(3) . ? C9 N3 1.312(3) . ? C9 C10 1.492(4) . ? C1 N1 1.353(3) . ? C1 C2 1.396(4) . ? C2 H2 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N2 H2A 0.80(3) . ? N1 H1B 0.82(3) . ? N1 H1A 0.89(4) . ? N3 H3A 0.84(3) . ? N3 H3B 0.81(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.23(12) . . ? O2 S1 N2 103.43(13) . . ? O1 S1 N2 108.45(12) . . ? O2 S1 C4 110.04(12) . . ? O1 S1 C4 109.17(11) . . ? N2 S1 C4 105.56(12) . . ? C5 C4 C3 119.5(2) . . ? C5 C4 S1 120.22(19) . . ? C3 C4 S1 120.24(19) . . ? O3 C7 N2 121.4(3) . . ? O3 C7 C8 123.0(3) . . ? N2 C7 C8 115.5(3) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C6 C1 120.8(2) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O4 C9 N3 122.6(3) . . ? O4 C9 C10 120.5(2) . . ? N3 C9 C10 116.9(3) . . ? N1 C1 C6 120.5(3) . . ? N1 C1 C2 121.1(3) . . ? C6 C1 C2 118.4(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 N2 S1 124.2(2) . . ? C7 N2 H2A 118(2) . . ? S1 N2 H2A 118(2) . . ? C1 N1 H1B 120(2) . . ? C1 N1 H1A 115(2) . . ? H1B N1 H1A 124(3) . . ? C9 N3 H3A 120(2) . . ? C9 N3 H3B 120(2) . . ? H3A N3 H3B 119(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 941618'